Showing Compound 1,2,2'-Trisinapoylgentiobioside (FDB021009)

Record Information

Version

1.0

Creation date

2010-04-08 22:15:24 UTC

Update date

2019-11-26 03:19:45 UTC

Primary ID

FDB021009

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

1,2,2'-Trisinapoylgentiobioside

Description

1,2,2'-Trisinapoylgentiobioside belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives. 1,2,2'-Trisinapoylgentiobioside is found, on average, in the highest concentration within broccolis (Brassica oleracea var. italica). 1,2,2'-Trisinapoylgentiobioside has also been detected, but not quantified in, brassicas. This could make 1,2,2'-trisinapoylgentiobioside a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 1,2,2'-Trisinapoylgentiobioside.

CAS Number

155380-01-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Show entries

Search:

Synonym	Source
1,2,2'-Trisinapoylgentiobioside	db_source
2-{[3,4-dihydroxy-5,6-bis({[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy})oxan-2-yl]methoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid	HMDB

Showing 1 to 2 of 2 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.058 g/L	ALOGPS
logP	2.84	ALOGPS
logP	2.54	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	8.81	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	323.81 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	231.76 m³·mol⁻¹	ChemAxon
Polarizability	96.49 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C45H52O23

IUPAC name

6-{[(4,5-dihydroxy-3-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}-6-(hydroxymethyl)oxan-2-yl)oxy]methyl}-4,5-dihydroxy-3-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}oxan-2-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

InChI Identifier

InChI=1S/C45H52O23/c1-57-24-13-21(14-25(58-2)35(24)50)7-10-32(47)66-42-40(55)38(53)30(19-46)64-44(42)63-20-31-39(54)41(56)43(67-33(48)11-8-22-15-26(59-3)36(51)27(16-22)60-4)45(65-31)68-34(49)12-9-23-17-28(61-5)37(52)29(18-23)62-6/h7-18,30-31,38-46,50-56H,19-20H2,1-6H3/b10-7+,11-8+,12-9+

InChI Key

HVHNDGOZMSAQDC-SRDSWEMOSA-N

Isomeric SMILES

COC1=CC(\C=C\C(=O)OC2OC(COC3OC(CO)C(O)C(O)C3OC(=O)\C=C\C3=CC(OC)=C(O)C(OC)=C3)C(O)C(O)C2OC(=O)\C=C\C2=CC(OC)=C(O)C(OC)=C2)=CC(OC)=C1O

Average Molecular Weight

960.8806

Monoisotopic Molecular Weight

960.28993797

Classification

Description

Belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acid glycosides

Alternative Parents

Substituents

Hydroxycinnamic acid glycoside
O-cinnamoyl glycoside
Coumaric acid or derivatives
Cinnamic acid ester
Disaccharide
Glycosyl compound
O-glycosyl compound
M-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Tricarboxylic acid or derivatives
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
Alkyl aryl ether
Fatty acid ester
Phenol
Oxane
Benzenoid
Monocyclic benzene moiety
Fatty acyl
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Acetal
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Ether
Primary alcohol
Carbonyl group
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Source:

Food

Biological:

Plant

Role

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Show entries

Search:

Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 56.25%; H 5.45%; O 38.30%	DFC
Melting Point	Mp 155-158°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052u-0041030905-488156d433b4c849caa1	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a7u-0196070604-5b0c09ccc992abdbb164	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05s1-0154070922-964dc29ea9eee5d858d6	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0abi-0092011704-b6efc5f7262894214506	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dr-0292040602-6f70e08ae89e7bb4a36c	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-0290000000-046277b57e1c16840dc4	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-06vi-0151000109-80599f98a0665872ab32	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-0971010012-55840c0421844be82526	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0571-1974031171-da467c5be648227ca614	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ab9-0190000101-43eb29a798b13204c9b9	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a73-0761010459-16cfe404405560661832	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05bu-1431000191-93f211a29acb26a1da68	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

512

DrugBank ID

Not Available

HMDB ID

HMDB41127

CRC / DFC (Dictionary of Food Compounds) ID

CPD88-P:NJK55-N

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Show entries

Search:

Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.

Showing Compound 1,2,2'-Trisinapoylgentiobioside (FDB021009)

Structure for FDB021009 (1,2,2'-Trisinapoylgentiobioside)